These questions may be an acquired taste. I quite enjoy interesting conversations.
- What would constitute a “perfect” day for you?
- For what in your life do you feel most grateful?
- What is something you’re proud of yourself for?
- What in life do you get truly excited about?
- What’s one thing you can’t live without?
- What are the chapters of your life?
- How does the way you see yourself differ from the way other people see you
- For example, are there places where other people would make really bad predictions about your actions? your preferences?
- Who is your best next-token predictor?
- Give me some good advice
- What’s some good advice you’ve received?
- Do you have any really good systems?
- How do you avoid freaking out about scary things?
- What is fun worth?
- What are the best emotions? The worst?
- What would you do if I gave you 20 dollars and you had to spend it today?
- What do you think are some big societal problems?
- Who are some of the best people you know, in terms of:
- altruism
- health
- habits
- giving advice
- being nice to be around
- Is doing good likely to lead to happiness?
- What is a fun tradition that you have, or want to create (with yourself, or with a friend)?
- Who looks up to you?
- What is a dream you’ve let go of?
- Are you lying to yourself about anything?
- What lesson took you the longest to unlearn?
- What is something you wouldn’t want to change about yourself?
- What question are you trying to answer most in your life right now?
- In what areas are you currently trying to improve?
- What do you value in friendships? What are the best ways they add to your life?